With a Little Help
by malaleen
Summary: The development of a relationship is never easy, especially if you're Jefferson. Watch his relationship with Emma develop through the eyes of a friend, Ruby Lucas. Ruby's POV


**Author's Note:** I'd like to start by thanking Batsonthebrain from Tumblr who gave me a fic prompt for a Mad Swan fic ages ago that has been percolating in my brain ever since: _Mad Swan first date at Granny's with Ruby's POV_. I didn't fit in the commentary to Belle, but I think I expanded the idea enough so you should be satisfied.

This fic is set as a sort of AU of S2 starting after episode 2 and picks up quite a bit after that point, bringing in elements and speculation beyond what's been seen. I also mention two other Emma ships in this fic, and tried to give realistic yet respectful reasoning as two why they wouldn't work over Mad Swan. Hopefully no one will be upset over the sinking of a favored ship for Jefferson and Emma.

Lastly, this is a very odd way of telling a story with Mad Swan. It's completely focused on their relationship, but through the eyes of Ruby Lucas. So much of what's happening is indirect and off page.

* * *

The first time Ruby saw him was when he was running away from Charming after the disastrous town meeting where Regina revealed she had regained her powers. At the time, she had little time to think about the strange man running away from David when the town's people were threatening to cross the line and their leader/prince was too obsessed with finding his family to do something about it. It was only later when David had talked down the town's people's panic and retrieved Henry from Regina's clutches that she learned about the owner of the destroyed portal and his inability to rescue Mary Margaret and Emma.

A week later, she was formally introduced to him when he and a young girl walked into Granny's. Trying not to be nosy like her Granny always accused her of being, she casually walked over to their table to take their order and introduce herself properly. "Afternoon to you. I haven't seen the two of you around lately. My name's Ruby."

The man looked up at her with a small smile and replied, "Afternoon to you too, Ruby. I'm Jefferson and this young lady is my daughter, Grace." At that admission, both father and daughter broke out in happy smiles.

Ruby couldn't help herself and smiled in return. "So Jefferson and Grace, what can I get for the two of you this afternoon?"

"We'd like two chocolate sundaes, please. And two cups of Earl Grey tea, with lemon and honey," Jefferson replied, smiling fondly at his daughter.

"Two sundaes and two Earl Grey's, coming right up," Ruby smiled, walking away to begin filling the order. She casually watched the two of them talk enthusiastically to each other, only pausing while she brought the ice cream and tea to the table.

A little while later, David and Henry walked into the diner, and Grace called out Henry from where she was sitting with her father. "Henry, come meet my papa!"

Henry looked at David for approval before running off to booth where Jefferson and Grace sat. David sat at the counter in front of her, looking back at Henry happily talking with both Jefferson and Grace. "I'm not sure I like him talking with that man," David admitted in low voice.

"He's the portal jumper you told me about, right?" Ruby asked, curious. "He seems harmless enough, and apparently is reunited with his daughter."

"I suppose," David grudging admitted. "I just wish he could have been more help with finding Emma and Mary Margaret."

A voice behind him spoke up, causing both Ruby and David to look at him. "I would have helped if I could have. But I don't have a working portal, and unless you can find me another one to use, I'm of no help to you."

David sighed heavily, "I know. I just want my family back so badly."

"Believe me, I understand. I waited more than 28 years to be reunited with mine," Jefferson said with a sad look on his face.

"But you're with your daughter now," Ruby pointed out, nodding towards the two children talking happily back in Jefferson's booth.

"All thanks to your grandson," Jefferson admitted, looking at Charming with a grateful expression. "He's got a lot of nerve, that boy."

David looked fondly at his grandson, who waved enthusiastically at him. "He does."

"Gramps, come meet Paige…I mean, Grace!" Henry looked apologetically at Grace. "Sorry, I forgot."

"It's okay, Henry," she said.

After that moment, a tentative friendship was borne between Jefferson's family and Charming's. Over the next few weeks before Emma and Mary Margaret's return, occasionally the two pairs would run into each other in town and Jefferson and Charming would attempt at making small talk while the two children chatted like best friends. Henry would eagerly tell Grace of the progress they were making in finding his mother and grandmother, and Ruby started to notice Jefferson not so casually trying to listen in on their conversations.

Her suspicions regarding Jefferson were soon confirmed after the miraculous return of Mary Margaret and Emma. It didn't take long for Ruby to notice that soon Jefferson and Grace would show up for breakfast at the diner around the same time as Emma and Henry occasionally, and of course, the two children would beg their parents to share the meal with each other. She would also notice Jefferson watching Emma far closer than a friend should when they were together, and how he would stare after her when she left to go to work at the station.

* * *

After a few weeks of this behavior, Ruby felt she needed to say something. After another morning of longing stares and awkward conversations, Ruby slipped into the booth after Emma left to walk the children to the bus and sat facing Jefferson. "You know, she probably wouldn't mind if you asked her out."

Jefferson turned to look at her in surprise. "What? No. I couldn't. She wouldn't."

"She might," Ruby said, giving him a knowing look. "Won't know unless you try."

Jefferson looked out the window, a sad expression crossing his face. "I very much doubt it. I'm afraid I made a really bad impression on Emma the first time I met her."

"What do you mean?" Ruby asked curiously, as Emma had never given her the impression she _didn't_ like Jefferson.

"Let's just say, I made several errors in judgment while attempting to reunite with my daughter," he sighed. "I wasn't affected by the curse like everyone else."

"Oh?" Ruby asked, curious as to what he meant. In many ways, while the curse took away her true self, it also allowed her to forget her painful past as well.

Jefferson gave her an appraising look, and must have found something in her expression that told him he could trust her with a few of his secrets. "As you might have heard, I'm the Mad Hatter from the Alice in Wonderland stories."

"Yes," Ruby agreed, having heard the rumors around town as to who Jefferson was in the Enchanted Forest. "It doesn't matter to me in the least, Jefferson. Many of us have pasts we're not proud of."

"You see, the time spent in Wonderland drove me to madness. Regina trapped me in Wonderland away from my daughter for about two years time in the Enchanted Forest," he explained sadly. "But time moves differently in Wonderland. No one but those who've been there realize this."

Ruby gazed at Jefferson with sad eyes. "You've been apart from your daughter for a lot longer than the 28 years you told David about."

"You could probably double that number and it'd be closer to being right," he sighed. "As a result of being trapped by the Queen of Hearts and being forced to do her bidding, it literally drove me as mad as the title says. And when the curse brought me here, my fractured mind couldn't accept the curse properly, not that Regina cared. So for the past 28 years, I had two conflicting realities in my head, driving me further insane that I was before. Not to mention Regina thought it would be funny to saddle me with a personality that had mental issues like agoraphobia. So I was trapped in that house without access to my daughter until Emma came, and started to break the curse."

Ruby's heart dropped as she heard Jefferson's story, and she thought she had problems with her past. "So what did you do to Emma?"

"I kidnapped her and Mary Margaret."

"What?" Ruby cried out, disbelief on her face.

"I wanted Emma to make me a new hat, one that had magic," he explained with a sigh. "I recognized she had magic, you see, and I was desperate to leave this cursed realm with my daughter."

Ruby ignored for now the question of how he knew Emma might have had magic when he was trapped in his home by the curse. "I take it your plan didn't work?"

"Ah, no," he chuckled lowly. "Emma bashed me over the head with a telescope and Mary Margaret kicked me out of a window."

Inwardly Ruby cheered for her friends triumphing over this adversity. "I see how you might think Emma might not be interested in more of a relationship with you, Jefferson," she said slowly, "but I still think Emma isn't as unreceptive as you think."

"But there's more," he added, sadness written all over his face. "She'll never forgive me when I tell her."

"Well, you'll never know until you try," Ruby coaxed, and looked up at the bell ringing over the door. Emma walked into the diner once again. Emma gave Ruby a curious look. Nodding towards her, Ruby said, "Maybe you should start now." And with that thought, she got up and walked over to the far counter, watching Emma take her spot once again.

Jefferson looked at Ruby for a long moment, and then nodded solemnly. Turning to face Emma, he began to talk intently to her. For the next several minutes, it was quiet in the diner, as Emma and Jefferson were the only two customers present. Then Ruby heard Emma shout, "You did what?"

Ruby looked up to see Emma standing beside the booth, anger rolling off her. "I can't believe you'd risk my life, and ultimately my son's life for the possibility of a bargain with Regina of all people."

Jefferson stood as well, moving towards Emma. "Emma I'm sorry, but you know how desperate—"

"Oh, I know exactly how desperate you were, Jefferson," Emma interrupted. "Stay away from me, and stay away from my kid."

"But Emma, Grace and Henry," he pleaded, reaching towards her.

"Grace is welcome to visit Henry at our loft whenever she likes," Emma said coldly, stepping back from him. "You are not."

"Alright," he whispered softly, and watched sadly as Emma stormed out of the restaurant. Jefferson looked up at Ruby, who looked on with worried eyes. "Went about as I expected. I'll be seeing you, Ruby. Thanks for listening." And with that said, he slowly left the diner.

* * *

For the next several weeks, Ruby saw very little of Jefferson and Grace around town. Of course, Storybrooke was in for some very unexpected and unwelcome excitement. New residents in the form of Cora and Captain Hook, the faked death of Archie, Belle losing her memories, and a out of town stranger left little time for Ruby to worry about Jefferson and Emma's stalled relationship. It wasn't until after Emma returned with Gold after finding his son, Baelfire, that Ruby started to see Jefferson in the diner again, and he was distinctly unhappy with the turn of events.

Once again, he and Grace began timing their breakfasts to coincide with Emma's and Henry's, only more often than not, they were seldom alone. On several occasions, Baelfire, who now went by the name Neal and ended up being Henry's missing father, joined them for breakfast. And a few times, a certain rogue pirate seemed to show up at just the right time to entertain Henry and to annoy Emma. Apparently, Jefferson now found himself in a three way race for Emma's affections, competing with the dashing Captain and Henry's father.

After yet another morning of dealing with both Neal and Hook, Emma as usual stomped off in a huff after Henry and Grace left for school, leaving Jefferson sitting behind at the diner's counter, looking thoroughly put out and depressed.

"Jefferson," Ruby said, nudging Jefferson in the arm. "You should throw your hat in the ring, so to speak."

Jefferson just gave Ruby a withering look, and said dryly, "Ha, ha. Very funny, Ruby."

"I'm serious," she insisted. "I really think you should consider it."

Jefferson just rolled his eyes, and got up to leave. "I'll see you later, Ruby. Thanks for the breakfast and the friendly conversation."

She smiled at him fondly as she watched him leave. Once again, she saw him longingly look towards the Sheriff's station, before turning to his car and heading home. Ruby tilted her head, and decided maybe it was time to work on this problem from another angle.

* * *

Three hours later, she was holding a couple of bags of takeout food for Emma and David at the station. She was resolved that she would finally talk to Emma about her relationship issues. Walking into the building she saw David sitting at his desk, going over some files, and Emma was nowhere to be seen.

"Ruby," David smiled up at her. "Just in time. I was dying for one of Granny's cheeseburgers and fries."

"I have Emma's grilled cheese and fries too. Is she here?" Ruby inquired, looking around for the blond sheriff.

"She's back in the interrogation room. Don't tell her I told you this, but I'm pretty sure she's hiding out," David said in an annoyed tone. It was a fairly well known fact that neither Snow nor David approved of either of Emma's persistent suitors.

"Ah, Hook or Neal?"

"Both, yet again," David confirmed. "Go on back. She'll be happy to see someone who's not trying to fight for her attention."

Ruby nodded and followed the hallway towards the back room. Knocking on the door, she waited for Emma to respond.

"If it's either of you two idiots again, I swear I'm going to kick both of your asses back to Neverland and New York," Emma called out in an annoyed tone.

"It's me, Ruby," she called out, "I have your grilled cheese and fries from Granny's."

Emma opened the door open quickly and pulled Ruby inside. "Oh thank god. I was starving, but I was afraid I'd run into either of those two jackasses if I dared leave this room."

"Rough day?" Ruby asked with a smile, handing over the food to Emma. She took a seat across from her at the interrogation table.

"You have no idea," Emma sighed, taking a bite of her grilled cheese. "I am so sick of the two of them fighting for my attention."

Ruby raised an eyebrow at Emma. "Because having handsome men fighting over you is such an annoyance."

Emma put down her sandwich. "I hate talking about, even hell thinking about, my romantic relationships, but I am in such a messed up situation right now and I have no one in town I feel comfortable enough to talk about it with. I mean, I used to talk to Mary Margaret before the curse broke, but now it's a little awkward, you know?"

Ruby nodded. She could see how Emma would have limited options for friendly confidences. "I'm all ears," she said with a grin.

Emma sat for a moment considering her alternatives, and finally admitted, "It's just, neither of them are really the best fit for me, you know?"

Ruby sat back in her chair. "What do you mean?"

Emma took another bite of her sandwich as she considered what to say next. "What Neal and I had together was over twelve years ago. He pretty much lost his chance with me the minute he let me take the fall for his crime. I know August was involved somehow, but still, I can't really let him back into my life in that way again. We can be friends, I think, but never anything more." She was silent for a few moments, then continued. "Thank god Henry understands that while Neal will always be his father, we're never going to be a true family together."

Ruby nodded, and then asked, "And Hook?"

Emma sighed at closed her eyes. "Captain Hook is very easy on the eyes, and I'll admit I'm damned attracted to the man."

"But?" Ruby prompted.

"He's never going to be the kind of man I'd need him to be when it comes to Henry," Emma explained honestly. "He talks about going out to sea here in this realm, and how much he thinks I'd enjoy traveling the world with him. I'll be honest, Ruby. If I didn't have a kid and family, I'd be sorely tempted. The thought of living life with no responsibilities is enticing."

"But you _do_ have responsibilities," Ruby said.

"I do," Emma agreed, "and I finally have the family I've longed for. I doubt Killian could stay in one place long enough to be truly happy here." Ruby raised an eyebrow at Emma's casual use of Hook's real name. "Not to mention the whole mess with him, Gold and Neal. It's just one big cluster fuck." Emma shook her head and resumed eating her sandwich.

"So neither guy is really in the running for boyfriend of the year, huh?" Ruby asked, innocently.

"Complete understatement," Emma agreed.

"So there's no man here in Storybrooke you could ever see yourself with?" Ruby prompted, giving Emma the eye. Hopefully she could find out whether or not she was right in pushing Jefferson into the running for Emma's heart.

Emma was silent for a long time, eating quietly and not answering Ruby's question. To be honest, Ruby thought she had pushed Emma too far, and she had reached the end of Emma's romantic confidences. To her surprise, Emma responded quietly. "For a while, there was someone I had considered briefly before this mess with Neal and Hook exploded."

Now Ruby was getting somewhere. She was positive Emma was referring to Jefferson, but the trick would be to get Emma to admit to it. "And now?"

"I don't know," Emma sighed, dropping her head into her hands. "There's a definite past between us, and he's done things that for a long while I never thought I could forgive."

"But?" Ruby prompted.

"But in many ways, he's a better match for me that either Killian or Neal. He'd be able to be a proper father to Henry, if things progressed to that point, and he'd treat me right. I just know it," Emma whispered. "He'd never leave me."

Ruby was silent for a few moments before she stood up. Before she left, she said a few parting thoughts for Emma to consider. "Emma, I know letting people into your life isn't something that comes easy to you. Believe me, I understand having troubled relationships, but I'm going to be honest. If you gave Jefferson just the slightest indication you'd be interested, I think you'd be surprised at how much he'd want to be a part of your life."

Ruby left Emma sitting there with a thoughtful expression on her face. She had done her part, and now it was up to Emma and Jefferson to do the rest.

* * *

A week later, a very interesting sight came into Granny's Diner for breakfast. Jefferson, Grace, Emma and Henry all walked in together, almost like a family would. Emma and Jefferson walked closely next to one another, nearly touching as they walked. They followed at a more sedate pace after the children, and sat next to each other in the booth across from Henry and Grace. Ruby walked up the group to take their orders. "Morning all! What can I get for you this fine day?"

Henry was quick to respond. "I'll have French Toast and bacon, please. And a cup of hot cocoa with cinnamon." He turned to Grace. "You need to try the cocoa here Grace. And it's awesome with some cinnamon."

Grace smiled back at Henry. "Thanks for the suggestion, Henry, but I like to have tea like my papa in the morning. Maybe I'll try it some other time." She smiled at Jefferson then looked up at Ruby. "I'll have pancakes and an Earl Grey tea with lemon and honey, please."

"Sure thing, kids," Ruby smiled at both, jotting down their requests. "And you Emma, Jefferson?"

Jefferson spoke up. "I'll have the tea, same as my daughter, and the French Toast and bacon, just like Henry."

"And I'll have the cocoa like my son," Emma added, smiling broadly. "But I'll have pancakes like Grace."

Ruby's grin nearly split her face, she was so amused at the group's orders. "Coming right up."

She started to walk back towards the kitchen, nearly wanting to jump for joy over her match making success, when she heard Jefferson call out to her. She turned and Jefferson merely returned her smile, simply saying, "thanks," and then leaned in to quickly kiss Emma. Henry and Grace just groan playfully at their parents actions. Emma gave Ruby thumbs up and also mouthed, "thanks" to her as well.

Ruby walked away from the newly forming family, happy that her interference had brought love and happiness to her friends. She could always brag that it was she who had witnessed the birth of their romance and future happiness.


End file.
